Nitromethane → trans-4-Methoxy-beta-nitrostyrene

HRID 1685325Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1685325
[CH:1](=O)[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[N+:11]([CH3:14])([O-:13])=[O:12].[OH-].[Na+]>CO>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2](/[CH:1]=[CH:14]/[N+:11]([O-:13])=[O:12])=[CH:3][CH:4]=1

Komponenten

5

Edukt 3

HCID 6375NitromethaneHCID 14798Sodium HydroxideHCID 312444-Methoxybenzaldehyde

Produkt 1

HCID 697963trans-4-Methoxy-beta-nitrostyrene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a cool (0° C.), stirred solution of 4-anisaldehyde (1.75 mL, 14.3 mmol), nitromethane (2.0 mL, 36.9 mmol) in MeOH (6.0 mL) was added NaOH (1M, 40 mL), and allowed to warm to room temperature. After 2.5 hours, ice water was added with stirring, extracted with DCM (3×), the combined extracts were dried (MgSO4), filtered, concentrated and purified on Biotage Horizon to provide the product as a solid: 1H NMR (400 MHz, CDCl3) δ ppm: 7.97 (1H, d, J=13.64 Hz), 7.51 (1H, d, J=13.64 Hz), 7.50 (1H, d, J=8.84 Hz), 6.95 (2H, d, J=8.84 Hz), 3.86 (3H, s).

Aufarbeitung

  1. temperatureto warm to room temperature
  2. extractionextracted with DCM (3×)
  3. dry with materialthe combined extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified on Biotage Horizon

Quellen und Nachweise

ORD-Eintrag
ord-347940af409348a9af43ff783f282a1a
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148400B2

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